Reaction #355758

Reaction equation

phenothiazine

iodoethane

potassium hydroxide

→

10-Ethylphenothiazine

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturewas refluxed for 24 hours
2. 2
   TemperatureAfter cooling
3. 3
   Filtrationthe reaction mixture was filtered
4. 4
   Otherthe solvent was evaporated
5. 5
   OtherThe product was recrystallized from methanol
6. 6
   Otherwas 103-104° C

Procedure

A mixture of 10 g (0.05 mol) of phenothiazine (obtained from Fluka), 11.7 g (0.075 mol) of iodoethane (obtained from Aldrich), 4.2 g (0.075 mol) of potassium hydroxide and 0.25 g of tetra-n-butylammonium hydrogen sulfate (obtained from Aldrich) in 200 ml of dry toluene was refluxed for 24 hours. After cooling, the reaction mixture was filtered and the solvent was evaporated. The product was recrystallized from methanol. The yield of 10-ethylphenothiazine (C14H13NS, FW=227.33) was 90%. The melting point of the product was 103-104° C. The 1H-NMR spectrum (100 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 1.40 (t, J=7.0 Hz, 3H, CH3); 3.90 (q, J=7.0 Hz, 2H, CH2); 6.78-7.32 (m, 8H, Ar).

Source